Windham Holiday Rentals, New York: Private House Rentals

A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

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Our top choices for Windham hotels

A log cabin with a deck, outdoor seating, and a view of a forest.

A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

A wooden covered bridge in a forested area with a paved path leading to it.

A cozy cabin interior with a stone fireplace, wooden walls, a dining area with a red and black checkered tablecloth, and a television mounted above the fireplace.

1. Hotel Vienna

Windham

Paul

2.732.572 ₫

3.400.231 ₫ total

includes taxes & fees

6 Oct - 7 Oct

A wooden cabin with a triangular roof, a wooden door, and a bench outside.

A round wooden table with a hanging light fixture, surrounded by four stools, set against a backdrop of a large window with a view of trees and a wooden deck.

A triangular wooden room with a bed and pillows, a window, and a view of a forested hill.

A bar area with wooden beams, a bar counter, and four bar stools.

2. Eastwind Windham

Windham

Sharon

6.527.129 ₫

7.839.068 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.

A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

3. Wylder Hotel Windham

Windham

Yousung

6.958.019 ₫

8.814.011 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A large, two-story house with multiple porches and string lights.

A room with a wooden floor, a chair, a lamp, and a view through a window with a decorative frame.

A grassy field with a wooden structure overhead, possibly a gazebo or pavilion.

A room with a wooden wardrobe, a bed, a nightstand, a lamp, and a fireplace.

4. Albergo Allegria Hotel

Windham

Roy

4.515.241 ₫

4.876.460 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

A bar with wooden chairs, a bar counter, and various bottles and glasses.

A wooden room with a bed, a nightstand with a lamp, and a wall with tree decorations.

5. Jimmy OConnors Windham Mountain Inn

Windham

Robin

3.859.070 ₫

4.167.794 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A two-story building with a balcony, surrounded by well-maintained lawns and trees.

A compact living space with a kitchen, dining area, and seating.

A view from a room with a glass door onto an outdoor patio. The patio has a metal table and two chairs, a small pumpkin decoration, and a metal fence.

A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

6. The Winwood Condominiums

Windham

Abdul

3.293.852 ₫

3.557.360 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

A wooden staircase leading to a second floor, a red sofa with floral cushions, and a wooden floor.

A covered outdoor seating area with wicker chairs and a table, surrounded by white railings and hanging planters.

A dining room with a wooden table, chairs, a chandelier, and a vase of flowers.

7. Antique Rose Inn Windham

Windham

David

3.508.245 ₫

3.788.905 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

A white door with a sign reading "BREAKFAST" above it, a thermometer, and a drawing of stacked cups with steam.

A grassy field with a bench and a mountain in the background.

A hotel room with two beds, wooden paneling on the walls, and two framed pictures.

8. Cave Mountain Motel

Windham

Nancy

3.612.193 ₫

3.901.168 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A bedroom with a large window, a bed, and a view of a forest.

A wooden cabin with a door, surrounded by greenery and a stone pathway.

A large, multi-story wooden house with a snow-covered roof and several lit windows, surrounded by bare trees and snow.

A spacious living room with a stone fireplace, wooden staircase, and modern furniture.

9. The Haüs Windham

Windham

Erica

3.211.586 ₫

7.366.302 ₫ total

includes taxes & fees

7 Oct - 8 Oct

A multi-story building with outdoor seating and a stone-paved patio.

A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

10. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Ryan

4.633.894 ₫

5.518.109 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

A wooden deck with a table and chairs, a glass door leading to a room with a dresser and a lamp.

A bedroom with a fireplace, a wooden ceiling, and a view of the outdoors.

A wooden-paneled bedroom with a bed, bedside tables, and a hanging light fixture.

11. Hotel Mountain Brook

Tannersville

Kristen

6.080.958 ₫

6.567.435 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A park with Adirondack chairs and a table, surrounded by trees.

A vintage car parked in front of a house surrounded by trees.

A well-lit hallway with a wooden staircase, a decorative vase, and a dining area with a table and chairs.

A lamp post in a grassy area with autumn foliage in the background.

12. Mountain Treasure B&B

Maplecrest

Daniel

4.313.842 ₫

4.658.949 ₫ total

includes taxes & fees

20 Oct - 21 Oct

13. Windham NY Escape

Hensonville

Miguel

11.148.423 ₫

14.093.270 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

A circular fire pit with chairs around it, set on a grassy area with a wooden fence and trees in the background.

A bedroom with a large window offering a view of a forested mountain.

A modern living room with a large window, a blue sofa, a wooden coffee table, and a rustic wooden wall.

14. Hunter Lodge, a Bluebird by Lark

Hunter

Shubhangi

3.512.143 ₫

4.354.432 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A room with a view of a landscape through a window, a chair, a table with a laptop, and a bed with books on it.

A staircase leading to a room with a stone floor, a potted plant, and a wooden chair.

A chair with a blanket, a potted plant, and a view of a snowy landscape through a glass door.

A spacious living area with a wooden floor, leather sofas, and a dining table.

15. The Perch Hotel

East Windham

Jason

6.218.624 ₫

6.716.114 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.

A bed with white linens and a woven pillow, a window with a view of trees and a wooden structure, and a wall-mounted light fixture.

A modern house with a large garage and a vintage camper parked in the driveway.

A modern house with a sloped roof, large windows, and a well-maintained lawn.

16. AutoCamp Catskills

Saugerties

Raquel

3.291.254 ₫

4.704.894 ₫ total

includes taxes & fees

4 Nov - 5 Nov

A bathroom with a shower curtain, a toilet, a sink, and a window.

A bathroom with three sinks, a trash can, and a chair.

A large tree in a grassy area with a small white building in the background.

A room with two beds, wooden headboards, a red accent wall, and wooden flooring.

17. SunView Motel

Tannersville

Victoria

2.709.145 ₫

2.925.877 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

A cabin with a picnic table and chairs in a forest.

18. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Yeudin

4.183.907 ₫

5.641.259 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A covered porch with outdoor seating, a staircase, and potted plants.

A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

A cozy room with a white sofa, a wooden table with a lamp, and a chair with a patterned cushion. There's a reception desk with a computer and a sign that says "Welcome".

19. The Colonial Motel

Grand Gorge

Eric

2.315.442 ₫

2.546.985 ₫ total

includes taxes & fees

5 Oct - 6 Oct

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Stay near popular Windham attractions

Windham Mountain Resort

9.0/10 (313 reviews)

This four-season Catskills resort offers 54 trails across 285 skiable acres for all ability levels. Experience winter's pristine slopes or summer's mountain biking and golf on the championship course.

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Windham Country Club

8.4/10 (20 reviews)

Nestled in the Great Northern Catskills, Windham Country Club features an 18-hole course with mountain views and stream-side fairways. After your round, unwind at Mulligan's Pub with panoramic vistas of the peaks.

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Windham Vineyards and Winery

9.0/10 (15 reviews)

Nestled in the Catskills, The Vineyard at Windham offers tastings from New York's finest wine regions. Savour diverse selections on their outdoor terrace while taking in spectacular Windham Mountain views.

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Huntersfield State Forest

This serene 1,300-acre forest offers a mix of evergreen plantations and northern hardwood trees. Hike the designated trail to the summit lean-to for panoramic views of the majestic Catskill Mountains.

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Elm Ridge Wild Forest

Commune with nature and explore the great outdoors at Elm Ridge Wild Forest during your travels in Windham. Discover the mountain views and cafes in this relaxing area.

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Ashland Park

This serene community park offers peaceful green spaces perfect for picnics and casual strolls. Enjoy a quiet retreat in nature, where locals gather for leisure activities away from the bustle of everyday life.

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Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

See all hotels in Windham

Two skiers on a snowy slope with a valley and mountains in the background.

Top Windham Hotel Reviews

Spark by Hilton West Coxsackie

10/10 Excellent

"Clean and well maintained hotel."

Hotel Vienna

8/10 Good

"Very clean and well kept place. The pool area is lovely as well. The breakfast was mostly sugar stuff though… with lots of pastries and sweetened yogurts, and only caffeinated coffee available. Be sure to prepare accordingly if you have dietary restrictions. We enjoyed our stay and the location."

Howard Johnson by Wyndham Saugerties

10/10 Excellent

"The room was clean and staff very pleasant and helpful. I would stay again."

Urban Cowboy Lodge

8/10 Good

"The room was clean but a little smaller than we anticipated. Was hard to tell online. We did a tour of other available rooms would definitely choose differently next time. The property was amazing. We stayed during the week so it was so nice and quiet. We had the Japanese soaking tub which was great! We brought our dog and we were able to take her with us everywhere on the property. You’d never know that it was a pet friendly place as it is kept very clean. My ONLY negative comment would be that there is no where to get a meal that isn’t ridiculous expensive. I understand the limited menus in the area but everything was ridiculous expensive and very bougie food. Next time we would definitely pack some more snacks and food. Otherwise the place I awesome and worth the stay. We loved the robes! Wore them to our sauna appointment and then went and did a cold plunge in the river. So tranquil! We did not hook up the the WiFi so we stayed off grid for the three days we were there and that was just incredible. The staff were all super friendly and accommodating. What a fantastic place! Can’t wait to go back!"

AutoCamp Catskills

10/10 Excellent

"Absolutely loved our stay! The area is beautiful, the property is amazing and so well-maintained, and the friendly staff. This was our first time staying in a premium Airstream for both me and my hubby, and we were honestly amazed very clean too! Such a fun, unique, and awesome experience."

Jimmy OConnors Windham Mountain Inn

8/10 Good

"We had a wedding in the area and this place was perfect for our needs. There’s a bar to the front of the property, which was fun to hang out and play pool. The beds were comfortable and the rooms were clean."

The Haüs Windham

10/10 Excellent

"Fantastic definitely a wonderful escape"

The Winwood Condominiums

10/10 Excellent

"Very happy with the condo. Staff was helpful resolving minor tv issue. It was clean with small kitchenette area."

Kaatskill Mountain Club & Condos by Vail Resorts

10/10 Excellent

"Great stay, beautiful place"

More cheap stays in Windham

SunView Motel

5844 Main St Tannersville NY

2.709.145 ₫

2.925.877 ₫ total

5 Oct - 6 Oct

includes taxes & fees

Red Ranch Motel

4555 Route 32 Catskill NY

2.775.412 ₫

2.997.341 ₫ total

1 Nov - 2 Nov

includes taxes & fees

7.4/10 Good! (539 reviews)

Howard Johnson by Wyndham Saugerties

2764 Route 32 Saugerties NY

2.853.373 ₫

3.195.778 ₫ total

2 Nov - 3 Nov

includes taxes & fees

7.6/10 Good! (1,003 reviews)

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

2777 ROUTE 32 Saugerties NY

3.300.349 ₫

3.696.391 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Kaatskill Mountain Club & Condos by Vail Resorts

61 LIFTSIDE DR Hunter NY

4.633.894 ₫

5.518.109 ₫ total

2 Nov - 3 Nov

includes taxes & fees

9.2/10 Wonderful! (432 reviews)

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

282 Cairo Junction Rd Catskill NY

4.183.907 ₫

5.641.259 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Hotels in Windham with star rating

Frequently asked questions

What's the weather like in Windham?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.

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Book Hotels in Windham on Expedia.com

Find hotels in Windham, NY from 2.546.985 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windham

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windham hotels

1. Hotel Vienna

2. Eastwind Windham

3. Wylder Hotel Windham

4. Albergo Allegria Hotel

5. Jimmy OConnors Windham Mountain Inn

6. The Winwood Condominiums

7. Antique Rose Inn Windham

8. Cave Mountain Motel

9. The Haüs Windham

10. Kaatskill Mountain Club & Condos by Vail Resorts

11. Hotel Mountain Brook

12. Mountain Treasure B&B

13. Windham NY Escape

14. Hunter Lodge, a Bluebird by Lark

15. The Perch Hotel

16. AutoCamp Catskills

17. SunView Motel

18. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

19. The Colonial Motel

Stay near popular Windham attractions

Windham Mountain Resort

Windham Country Club

Windham Vineyards and Winery

Huntersfield State Forest

Elm Ridge Wild Forest

Ashland Park

Learn more about Windham

Top Windham Hotel Reviews

Spark by Hilton West Coxsackie

Hotel Vienna

Howard Johnson by Wyndham Saugerties

Urban Cowboy Lodge

AutoCamp Catskills

Jimmy OConnors Windham Mountain Inn

The Haüs Windham

The Winwood Condominiums

Kaatskill Mountain Club & Condos by Vail Resorts

More cheap stays in Windham

SunView Motel

Red Ranch Motel

Howard Johnson by Wyndham Saugerties

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Kaatskill Mountain Club & Condos by Vail Resorts

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Hotels in Windham with star rating

Frequently asked questions

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